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Boston to Portland/Yarmouth, Maine Coastal Roadtrip

We are flying to Boston on August 18. We will stay in Boston for 3 days and then do a coastal roadtrip to Portland (and then Yarmouth) Maine for an additional 3-4 days. I am looking for some type of itinerary or ideas of things to do along the way (activities, where to sleep, eat, etc.) for a late twenty-something couple. Thanks!

I'm too old to reply I suppose. There is much indeed to do/see and it all depends on interests (at your age). Do you like history, museums or is a beach and sailing more interesting? I'm sure others will pitch in with their ideas. We're fairly new in the Boston area but have done exploring in Maine as well as closer.

Portland has a lot of restaurants. Chowhound/northern New England is the best place to read restaurant suggestions. Do a search on Portland. We are more the mailboat on Casco Bay type so you might want to see if there are any recommendations for ocean kayaking. Kayaking of all types is very popular in New England. If you like beer, there are quite a few micro breweries in NH and Maine. You can do a beer tour in Portsmouth. You can also get ice cream trail, wine trail, etc maps for each state. Flag Hill Winery and Distillery in NH (a detour from the coast) makes wine as well as vodka.